120 Questions to ask a guy over text

One key element to having a long-lasting and perfect relationship with a man is having a good conversation. So many women find it difficult to keep a good conversation flow between their man and them. A good way to have the right conversation with your man is asking him the right question. Effective questions are known to open conversation topics and inspire deeper thought.

You have a very good chance with your man if you are very good at asking questions like this. But some women find it hard to generate these questions and they seek help.  That is why we have taken our time to gather 130 effective questions to ask your man. Meanwhile, you need to be ready for surprising answers. Asking your man these questions will help you know him better and of course, create more connections.

The first 110 questions are interesting questions you can ask any guy while chatting. The remaining 10 is good for when you two are planning to get married.

120 Questions to ask a guy over text 

questions to ask a guy over text

  1. What are you really good at?

This question helps to know your man’s strengths and weaknesses. You don’t want to go into a relationship, or rather, get married to a man that is even yet to discover his potential.


  1.   What was your last major accomplished goal?

Ask your man to tell you his past accomplished goal that he feels it is his major accomplishment. It is a very good way of opening deeper conversations and knowing his potentials.


  1. Why are you special?

People always believe that they are special and unique in their own different ways.  Ask your man why he thinks he is special and different from other people. It will help you to know him more.


  1. Is there something you’ve attempted severally however failed?

This is an interesting question to know your man’s previous failures and how he reacted to them. So many guys give up on things after failed attempts. Know how much it will take your man to give up on things by asking this question.


  1. Have you expected a bad result but came out the worst?

This is something that happens to people most of the time. You don’t know what answers this question might give. However, make sure your guy is in a good mood before you ask this question.


  1. How would you describe your opposite self?

All guys have an opposite side of themselves, this tends to show in them when they are angry or happy. If you can get to know your man’s opposite self, you will be able to manage him.


  1. What are your regrets?

This is a very deep question to open up a deep conversation. Asking your man this question will make you realize his gravest mistake that still fight him.


  1. What is your favorite quote?

People have a favorite quote and it may be what they live by. Asking your guy this question will let you know the kind of word that keeps him green.

  1. What makes you angry easily?

Every man has different things that can get them angry easily. It may be what people do or what happens without expectation. Asking your man this question might help you in keeping his cool.


  1. What bad decisions have you made but turned out right?

It is impossible for this to not occur in every man’s life. This is a very good topic to open with your man. Another thing is this question has the potential to bring about more topics.


  1. What is the most important thing you think you’ve done?

This is a simple question just to keep the conversation flowing. Get to know the most important thing your man has done.


  1. What would you like to be known as the best?

Fame is what most men wish for and you don’t know how they plan to get it. Asking your man this question will reveal his true ambition and zealousness.


  1. What is something most people get wrong?

Don’t believe the way you see things is the way other people see them. Some men have a different view to what most people see.


  1. Does anything get you worried easily?

There are so many reasons for men to be easily worried. Let your man have a feeling that you care about what worries him easily.


  1. Which unusual place do you visit often?

This is not an easy question to ask a man but it is good to know. Make sure your man is in a good mood before you ask him this question, it will help you to get a fair answer.


  1. What is your dream job?

The most likely answer to this question is yes because all men have a dream job. But try asking him what the dream job is to weigh his level of ambition.

  1. Have you ever thought you are good at something but turned out to be negative?

This is a usual bubble-bursting moment for most guys. It is a good question that can bring about a lively conversation.


  1. Is there anything you can’t do for money?

This is a deep and serious question to ask a man. There are different levels of desperation for money in men. It is good for every woman to know her man’s level of desperation for money.


  1. How do you think you can make the world better?

It is possible your man has the potential to be a good leader but doesn’t show it. Asking him this interesting question will tell you more about him and a chance for more flow.


  1. How do you think rich people live?

The question aims to know your man’s fantasies about money. Expect to get surprising replies after asking guys this question.


  1. What’s your vision in the next 5 years?

It is also important to know if your man has a plan or vision for himself for a better future.


  1. What are the things you do for fun?

This is another simple yet interesting question to ask a man. If you are the type of woman that loves to have fun a lot or you are just curious what your man do for fun, feel free to ask him about this.


  1. Do you like movies?

Just to keep the conversation flowing. If he has told you what he does for fun but movies is not one of them, ask him this question. Ask ‘why’ if the answer is ‘No’.


  1. Was your high school days perfect?

Here is another fun question to ask your man. The perfect high school days will be an interesting story to hear from your man. Don’t ask further if your man says no, there may be memories he wants to forget.


  1. What is your favorite food?

It isn’t a bad idea to ask your man what his favorite is. This can help you to prepare for his next visit to your house.


  1. Is there someone you never want to lose?

Every man has a special person they never want to lose in their life. Show your man some curiosity by asking him this interesting question.

  1. Do you like reading books?

This is another simple and effective question you can ask your man while chatting. Find out if he reads a lot and what he read the most.


  1. Which novel is the best you’ve read?

If your man reads a lot and he reads novels the most, ask him this question. But make sure you also read novels a lot so you don’t make the conversation boring.


  1. Who is your favorite author?

After asking his best novel ever and a little bit of chat on it, feel free to ask him who his best author. You may get another chance to keep the topic hot by asking him this.


  1. What is your favorite TV show?

If watching TV is part of what your man do for fun, ask him this question to find out what he watches most on TV. Some guys prefer news to reality shows or soap operas.


  1. What value do you give friendship?

Believe it or not, every man gives different values to friendship. It is a very good decision to ask a guy this question if you think you are already close friends.


  1. What’s wrong but sounds right to you?

We all have that one thing that every people see it as wrong but we feel it is right. You don’t know what the guy own is, so asking this question is a good topic opener.


  1. What is it you are poor at?

Even if the guy is the kind of Mr. Perfect guy, there must be something he is really not at. Either it is talents, skills or matters of heart, ask him what it really is.


  1. Is there anything you are tired of hearing?

What is it you think your guy is tired of hearing? Maybe you even say one of those statements and you don’t know. Finding out isn’t a crime.


  1. What is your behavior like when you are broke?

Men have different kinds of behavior when they are out of money. Some get angry, sad, and some even do things they don’t normally do. Find out what his behavior is like when he is broke.


  1. Ever spoilt a very expensive thing?

This question is very interesting and an uncommon question to ask a guy. You can create a long conversation with a guy by asking just this one question. I am sure he will tell you a lot of stories.


  1. What lessons have you learned from a past mistake?

Everybody makes one or more mistakes in their lifetime. The ability to learn from each mistake we make shows strength. Let your man share a story of his past mistake and his lesson.


  1. Do you judge people quickly?

Here is a very brilliant and important question to ask a man over text. Ask him this to get to know how quick your man judge other people.


  1. Do your emotions control you?

Hanging out with a guy that allows his emotions to control him can be difficult for ladies. So it is better you know the kind of guy you are dealing with.


  1. What kind of music do you listen to?

This is just another fun question to ask your guy over text. You may be lucky he likes what you like, it will boost the conversation.


  1. Who is your favorite artist?

After asking him what music he loves, ask him who his favorite artist is too.


  1. What is your dream country?

Having a dream country is common to most people. Find out which country your man wishes to live and ask him why he likes the country, you may be surprised by his response.


  1. Do you travel a lot?

It is not new that not all guys like to travel. Some see it as stress, waste of money, and time. If you are the type that travels a lot, ask him if he is in the same realm as you.


  1. How many countries have you been to?

If his answer to the previous question is yes, then it is time to know how many countries he has traveled too. Guys that explore tend to love fun.


  1. How well do you handle stress and pressure?

Guys that find it easy to handle stress and pressure are known to be the best for friendship or relationship. Trying to find out how good he is when he is stressed is not a crime, it will prolong the friendship.


  1. Where do you invest most of your money?

This is not about prying into his businesses, there is a level to which you will ask him this question. What he does with his money is something you should at least know a bit about. Ask him when there is fun in the atmosphere and don’t pester on it.


  1. Has anybody completely lost your respect, and why?

Asking a guy this question over text means you are trying to know what he doesn’t like. The guy will tell you the story if there is any, but it is advisable to learn and stay away from the particular reason if you value the relationship.

  1. What is your nemesis?

You can always avoid this question if he is not in the mood for a serious text. But if you feel he is in the mood, you can ask him this question to start up the conversation. Meanwhile, don’t laugh his story off, you will need to show some concern after he shares the story. 


  1. You have the chance to make a wish, what would it be?

This is for when the conversation is getting dry and you still feel you should continue. Ask him what his wish will be if he is given the chance to pick one. He will surely want to tell you what his wish is, and then you can get another conversation from that.


  1. What attracts you most in a woman?

Guys have different things they like in a woman, and you may not know what his own is. You can ask him if he has found that thing in you too.


  1. What has made you so scared but turned out to be no big deal?

The two of you will definitely have a reason to laugh hard after you ask him this question. This is good for some teasing later on.


  1. Have you taken advantage of anyone?

This is another serious question you may want to ask your man whenever you are into some serious chat. You can find out more by asking how he felt after taking the advantage.


  1. What’s cool about being a male?

Do you really know how cool it is to be a guy? This question will give you a chance to find out more. You should expect interesting and funny answers the guy will give you. You can further the question by asking what is not interesting about being a guy too.


  1. Has anything made you cry recently?

We know that something really serious and overwhelming must happen to a man before he can cry. If he has had any reason to cry in recent years, the incident might still be bothering his mind. Ask him what it is, and show him some concern with some consoling words.


  1. What is your most treasured possession?

Find out what he treasures most among all of his possessions and don’t hesitate to ask him why. You may be surprised at the answers he will give you.


  1. Which country do you plan to visit next?

If your man loves to travel a lot, you may ask him which country he has in his plan to visit next. You may further this by asking why he wishes to visit the country.


  1. Have you ever been given or do you have a pet name?

This is a very interesting question to give room for some teasing after the conversation. This will surely light up his and your mood after you find out the fun in having this conversation.


  1. What was the first impression you had of me?

You must definitely expect some sweet words or some funny answers after asking your man this question. You can also ask him if he has realized the first impression is wrong or remains right.


  1. Do you have a role model?

Do you even know who he is working on becoming like in the near future? This is a chance to know what the guy wants to become and his ambitions.

  1. How often do you get bored?

Guys that love to have fun a lot get bored easily and very often. Asking a guy this kind of question is a tricky way of knowing if he loves catching fun. Ask him what he does most of the time to kill the boredom.


  1. Do you listen to your heart or your brain?

This question can bring about a serious yet interesting conversation if you know the right way to ask a guy. You can further ask why he thinks it is better to listen to one rather than the other.


  1. What are your biggest weaknesses?

Every guy has one or more things that weaken their minds. The most important thing is that they love to share these things with women they trust. Feel free to ask the guy this question to find out what his weaknesses are.


  1. What would you do if you win the lottery tomorrow?

There are different kinds of plans for money in guys’ minds; some even spend the money without winning the lottery yet.  You don’t know what plans he has for this kind of opportunity but you really need to find out fast.


  1. You are given the chance to have one superpower, what would it be?

We all fantasize on having one or more superpowers. Whether his own is the ability to go back in time, the ability to see the future, you don’t know. Here is a chance for you to find out, and don’t hesitate to share yours too. You can also ask why he thinks the superpower is the best for him.


  1. Which earliest memory do you have?

This can be an interesting question for some fun or a serious one for a deep conversation. It all depends on the kind of response the guy gives.


  1. Has anyone walked on you naked?

One of the funniest stories you can get from a guy will come out of this question. If he is ready for some fun, he will tell you how it happened and how he felt after.


  1. What is your favorite season?

We all have that particular season we seem to be more active and happy in it. Let the guy tell you what his own is and ask him what he does to enjoy the season. It is just to bring up an interesting conversation.


  1. Do you like visiting your family often?

There is no big deal in trying to know how often he visits his family. This can help you know how much he thinks about them.


  1. Are you religious?

Finding out if the guy is religious is not a crime he would bite for. Ask him which religion he is into and why. You can also ask him if religion has affected his social life.


  1. What is your worst date ever?

This question has a lot of potential to create a long funny and interesting conversation between the guy and you.  He will certainly tell you the story and you will both laugh at it, you can also use this to tease him later on.


  1. What is your biggest fear about life?

There is no how a man won’t have a little bit of fear about something in this life. He would also love to share what the fear is if he thinks you are serious about the conversation. But you must be ready to be a problem solver.


  1. Do you connect with people easily?

This is a question that will give you a chance to get to know the guy better. You can also ask him if he has had a hard time connecting with people he likes so much.


  1. How do you start a conversation?

You already know how you start your own conversation with people. But how does he start his own with people? Well here is your chance to find out.


  1. Do you weirdly feel like you are being stalked?

This question is not for a funny conversation. You should expect a serious conversation when you ask a guy this question and he answers positively. Guys that feel like they are being followed all the time are so paranoid and find it hard to trust people.


  1. Has anything ever happened to you without explanation?

Another way to show some interest and care for the guy is asking this question. Whether it is a good thing or a bad thing, he will love to share the story.


  1. Have you ever been harassed or pulled over by a cop?

Well, this question has no serious motive. If all you want from the guy is to make you laugh a bit when you are bored, then ask him.


  1. Why do you like your best friend?

This is for if you need some tips on how to get closer to the guy. You can ask him to tell you about his friend and how they met. Then ask him why he likes the guy to make him his best friend.


  1. Have you ever stolen before?

If you want to get the most sincere answer from this question, you must make sure there is fun in the air and the two of you are in a good mood. It is a very tricky way to find out if you can trust him if you two just met.


  1. If you had to hide a treasure, where would you keep it?

Here is a kind of test question to ask a guy if you want to know how much trust he has in you. There is a chance that he doesn’t tell you where he actually keeps his treasured possessions. 


  1. Are you an optimist or a pessimist?

It is really good to ask a guy this question if you two just met and you want to know about him.


  1. Where would you go if you could travel back through time?

We all wish that we could travel back through time at some point. It is either to correct some mistakes or to refresh memory. You don’t know where the guy would wish to go to, but you always have the chance to ask him.


  1. How long have you fallen sick?

This is another question to add to the length of the conversation between your man and you. Ask him if he has any health issue and how this has affected his life.


  1. Have you ever gotten in an accident?

You can also ask him if he has gotten in an accident before. If his response is ‘several times’, ask him which was the worst and how badly he got injured. You can also ask him if he still has trauma from the accident.


  1. Have you ever felt like running away from trouble?

This will help in case you are having a feeling that he doesn’t have much courage as a man. You can stylishly get your answers by asking him this question.


  1. Are you a day guy or a night guy?

If you feel it is necessary to know when he is more active, you can ask him this question.


  1. Would you rather be rich and miserable or poor and happy?

Some people don’t care what comes after they get rich, all they want is the money. This question will help create a long conversation and it will also give you the chance to know him better.


  1. How would you live your life if you were told you have 3 months left to live? And what mistake would you correct?

This is another perfect question that combines the ability of long conversation with friendly interrogation. How do you think he will live if he has limited life left to live? Find out.


  1. What is your best trip ever?

Find out more about his fun lifestyle. Ask him where he traveled to and what made the trip the best ever. You both will surely have a reason to laugh during the conversation.


  1. Which memory makes you laugh when you remember? And why?

Memories that make a guy laugh whenever he remembers it is one of the funniest moments of his life. Let him share his story and how he feels whenever he remembers.


  1. What is your plan for after retirement?

If a guy already has this in his pan, it shows he is very reasonable and thinks a lot about his future. Has he told you everything about his plan while working? Well here is to tell you that you need to know his plan too after he has retired.


  1. How good are you with budgets?

You can also find out the answer to this question yourself if you take your time to monitor him. But it is best to find out from him directly too. If he is the guy you wish to spend your life with, then this question is important for you.


  1. What is your take on credit cards?

After he has told you how he does his budgets, it is time to ask him what his opinion is on having a credit card. This is another way to find out if he is really good with saving and budgets.


  1. Do you cry in the movies?

This is a seemingly funny question to ask a guy over text. But the truth is some guys cry in the movies. It shows the level of emotions and how it controls them.


  1. What is your take on gender equality?

This question can be for a serious discussion or just for fun, it depends on how you take it. But guys that believe in gender equality are believed to be the best to hang out with. They have greater respect for women.


  1. Are you into body fitness?

This is just an interesting question that can help you know a bit more about him. You can ask him the kind of exercises he does for fitness. You can also ask if he thinks you need to get into fitness too.


  1. How do you handle disagreements?

This is to find out if he conservative when he is in disagreement with people or he is aggressive. Guys that are really good at handling disagreements with people are best to hang out with for women. The reason being that disagreement always comes up between men and women.


  1. Have you ever committed a crime?

This question may be seen as background checking for some guys and they may be offensive about it. However, you may try asking when he is in a very good mood, it may do the trick. Ask him if he got away with it or he got his punishments.


  1. What’s your best and a worst household chore?

This one is for another need to have more conversation with the guy. Ask him about this interesting question and share your own best and worst too.


  1. Describe an ideal weekend for you?

There are so many types of an ideal weekend for a guy. Yours is to ask him which type of weekend is ideal for him, it will detail the things he loves doing in his leisure time.


  1. Do you prefer to be left alone when you are angry?

Some guys find it difficult to control their anger and that is why they prefer to be left alone when they are angry. Guys that love to have people calm them down when they are angry can tame their anger. You need to know which part he falls.


  1. What cheers you up on a bad day?

The reason you need to ask a guy this question is if you want to know what makes him happy at all times. It is a very reasonable question that can help strengthen your relationship.


  1. What is your dream house like? Describe it

For sure all guys have the kind of house they dream of having. Some guys like it small and beautiful while some like it super big and awesome. If you care to know whether you guys have the same idea on a dream house, here is your chance.


  1. Do you believe in superstitions?

Here is another question for more information on his personality. It is believed that superstitions affects people’s personality because it affects people’s belief. If you want to know more, ask him why he thinks superstition is real. He may have a real-life story to tell.


  1. What kindest thing have you done for someone?

Asking him the kindest thing he has done for someone is not a bad idea for more conversation with him. At least you should know the length at which he can help people. You can also ask him if he expected any reward from the person he helped.


  1. What kind of student were you in school?

Find out if he was the most serious, most stubborn, or the coolest student in school. It has no motive for a serious discussion but he may tell you a funny high school story.


  1. Which food has the best smell but tastes horrible?

Expect surprising and funny answers when you ask him this. Don’t be surprised if the food is actually one of your favorites. This is where you can prolong by arguing a bit.


  1. Which weird food do you like?

This is another way to get him to make you laugh. You can ask him why he like the food and how he makes it.


  1. What’s your favorite dessert?

This is a nice question but you won’t get much from him. You may ask him why he likes it so much. This can also be a tip for you in case he is visiting you very soon.


  1. Do you prefer coffee to tea?

There is absolutely no dumbness in asking this question. All you are doing is to know more of what he prefers. Get more of these questions to help you know his preferences.


  1. Do you think watching news is important?

This will help you judge how much of concern he has for matters going on around him. Most guys don’t care about what is going on in the news; it is not a crime though.


Questions to ask while in a long term relationship


This section contains questions you should ask a man after he has asked your hand for marriage. These questions are very important and you should take the conversation seriously.


  1. How romantic are you?

You deserve to hear how romantic he thinks he is even though you already have the answer in your mind. If you want a romantic man for a husband, this is important to ask.


  1. What was your parent’s marriage like?

This definitely has the most effect on how men behave after getting married. They learn most of the things they do from their parent’s marriage. If his parents have had the most enjoyable moments, then you will definitely enjoy him as a husband.


  1. Why did your last relationship end?

If he has told about his ex-girlfriend, ask him what happened that they ended the relationship. This will definitely help you in handling your marriage.


  1. How many kids do you wish to have?

This is a very important question that you can ask your man when you are both in a good mood. If he has asked your hand for marriage, then know what he feels about birth control. You need to know if you two are on the same page.


  1. What do you do that can make me question your loyalty?

A very nice way to ask your man if there are things he does that can later disturb your marriage. If you get all the sincere answers from him, you will be able to decide if he is the right man.


  1. Have you dreamt of a future with me?

This is a simple question to ask if you still doubt his love for you. You are just trying to know if he has something deep for you. Don’t take it as a crime if he is negative though.


  1. What is your belief about divorce?

Some men actually believe that threatening a woman with divorce when there is a little bit of disagreement is the best. You need to know if your man’s belief about divorce is what you can take.


  1. How do you think disagreements should be settled in a relationship (outside the relationship or within the relationship)?

A very crucial detail you should never leave out before you get married to a man. Make sure your man believe in what you believe in. But it is believed that perfect relationships can settle disagreements within.


  1. How will we compromise if we don’t have the same level of saving and spending?

Another brilliant way to be sure that you and your man are really on the same page. You should be sure that your man will be ready to compromise with you in situations like this. This helps for a long-lasting relationship.



  1. If one of your friends flirted with me and I tell you, how would you handle it? What if one of my friends flirted with you, would you tell me?

This question will let you two know how much you trust yourself. If you get the most sincere answer from the first question, it shows how much your man can go crazy for you. The second one will tell you how much your man can share with you. You should also tell him what you feel about the questions.



You should never allow your chat with a guy go dry. This gives men impressions that you will make the most boring girlfriend ever. It is very important to know how to keep the conversation flow high, it attracts guys.

Now that you have read all the comments on the questions you can ask a guy online, use these ideas to make the connection between you and your man grow.  We hope this works for you and enjoy your chat.